diff --git a/WORKSPACE b/WORKSPACE
index e65d3ad5e..7936eaee5 100644
--- a/WORKSPACE
+++ b/WORKSPACE
@@ -148,7 +148,7 @@ go_repository(
 ## field in this rule
 go_repository(
     name = "org_letsencrypt_pebble",
-    commit = "cdd3ed3ddfdf9da7ab27fbe1fe032d0865b65376",
+    commit = "2e69bb16af048c491720f23cb284fce685e65fec",
     importpath = "github.com/letsencrypt/pebble",
     build_external = "vendored",
     # Expose the generated go_default_library as 'public' visibility
@@ -162,7 +162,7 @@ container_pull(
     name = "io_kubernetes_ingress-nginx",
     registry = "quay.io",
     repository = "kubernetes-ingress-controller/nginx-ingress-controller",
-    tag = "0.21.0",
+    tag = "0.23.0",
 )
 
 container_pull(
diff --git a/hack/ci/lib/build_images.sh b/hack/ci/lib/build_images.sh
index a2c71eb8c..c77ec7c45 100755
--- a/hack/ci/lib/build_images.sh
+++ b/hack/ci/lib/build_images.sh
@@ -42,7 +42,7 @@ build_images() {
         "${DOCKER_REPO}"/cert-manager-acmesolver:"${DOCKER_TAG}" \
         "${DOCKER_REPO}"/cert-manager-webhook:"${DOCKER_TAG}" \
         "pebble:bazel" \
-        "quay.io/kubernetes-ingress-controller/nginx-ingress-controller:0.21.0" \
+        "quay.io/kubernetes-ingress-controller/nginx-ingress-controller:0.23.0" \
         "k8s.gcr.io/defaultbackend:bazel" \
         "vault:bazel" \
         "gcr.io/kubernetes-helm/tiller:bazel" \
diff --git a/test/e2e/BUILD.bazel b/test/e2e/BUILD.bazel
index fa29c767f..442ddd655 100644
--- a/test/e2e/BUILD.bazel
+++ b/test/e2e/BUILD.bazel
@@ -6,7 +6,7 @@ container_bundle(
     images = {
         # A set of images to bundle up into a single tarball.
         "pebble:bazel": "//test/e2e/charts/pebble:image",
-        "quay.io/kubernetes-ingress-controller/nginx-ingress-controller:0.21.0": "@io_kubernetes_ingress-nginx//image",
+        "quay.io/kubernetes-ingress-controller/nginx-ingress-controller:0.23.0": "@io_kubernetes_ingress-nginx//image",
         "k8s.gcr.io/defaultbackend:bazel": "@io_gcr_k8s_defaultbackend//image",
         "vault:bazel": "@com_hashicorp_vault//image",
         "gcr.io/kubernetes-helm/tiller:bazel": "@io_gcr_helm_tiller//image",
diff --git a/test/e2e/charts/BUILD.bazel b/test/e2e/charts/BUILD.bazel
index 92054e961..7de1f04ec 100644
--- a/test/e2e/charts/BUILD.bazel
+++ b/test/e2e/charts/BUILD.bazel
@@ -5,7 +5,7 @@ container_bundle(
     images = {
         # A set of images to bundle up into a single tarball.
         "pebble:bazel": "//test/e2e/charts/pebble:image",
-        "quay.io/kubernetes-ingress-controller/nginx-ingress-controller:0.21.0": "@io_kubernetes_ingress-nginx//image",
+        "quay.io/kubernetes-ingress-controller/nginx-ingress-controller:0.23.0": "@io_kubernetes_ingress-nginx//image",
         "k8s.gcr.io/defaultbackend:bazel": "@io_gcr_k8s_defaultbackend//image",
         "vault:bazel": "@com_hashicorp_vault//image",
         "gcr.io/kubernetes-helm/tiller:bazel": "@io_gcr_helm_tiller//image",
diff --git a/test/e2e/framework/addon/nginxingress/nginx.go b/test/e2e/framework/addon/nginxingress/nginx.go
index 618dfd08d..28dc962f9 100644
--- a/test/e2e/framework/addon/nginxingress/nginx.go
+++ b/test/e2e/framework/addon/nginxingress/nginx.go
@@ -100,7 +100,7 @@ func (n *Nginx) Setup(cfg *config.Config) error {
 			},
 			{
 				Key:   "controller.image.tag",
-				Value: "0.21.0",
+				Value: "0.23.0",
 			},
 			{
 				Key:   "defaultBackend.image.pullPolicy",